I like some of the ideas presented here. That said...
“It’s not a winning strategy, and it’s not the sure-fire sort of like zinger that Democrats think it is,” says Insha Rahman, the director of Vera Action, which advocates for criminal justice reform. “Calling Trump a convicted felon doesn’t really stick on him because he doesn’t fit the trope of what a convicted felon is, because it is a dog whistle—it is linking race and criminality.”
I disagree with this whole line of thought. I get this person has a good agenda but seeing everything through that lens I think blinds her to other perspectives.
I think it's good and powerful to call Trump a felon. It drives home a particular point to his base — that they are following a criminal. He's one of the bad guys and she's one of the good guys. Is it a nuanced message? No. There's a lot of good points she makes about messaging and framing. But I think it does hit home especially with low-information voters.
Furthermore, I think it highlights many of the points she wants to make with nuance, just very bluntly. Is there a racist connotation to the word felon? Well pointing out the white guy is a felon attacks that. Is there stigma about being a felon? Pointing out Trump is one undercuts, for some, that a felon can only be a violent criminal.
I just think it's a little silly to see people's positive reaction to that message and say, "No, this isn't going to help you win." But I agree with everything else.